Tuscan lifestyle bike tour

Welcome to the bike trip combining fantastic moderate rides and cooking lessons; we add special tasting: olive oil, wine and cheese. Of course is la cucina Toscana – simplicity in its purest form. Tuscany cooks take advantage of the freshest seasonal products and tamper with their natural state as little as possible. The cooking and the cycling aspects will please anyone who has a strong interest in one or both of these great passions.
You will explore gorgeous loop rides in the beautiful val d’orcia: Pienza, Montalcino, San Quirico. Across Val di Chiana to reach Cortona,  Discover Crete Senesi, a rolling sea of  land and sightsee Siena town.

How much cooking will we do?
After you have worked up an appetite, we will feed you very well! Most days include a hands-on cooking class or a visit to taste local food artisan. Our dining-out experiences range from a simple osteria, to a family trattoria, and an elegant restaurant. You will come home inspired, not only with new recipes, but also with the enthusiasm to cultivate these lessons into your lifestyle.

2017 Departure guarantee: June 17th & September 23rd


  • Return from your trip with actual know-how to create a Tuscan dinner back home—it’s the ultimate keepsake!
  • Pedal rolling hills past Sangiovese vineyards
  • Brunello wine tasting at acclaimed bike oriented winery Ciacci Piccolomini

Saturday : Welcome to Villa Le

Private van transfer to the villa, 2 km from Monticchiello, in time for the welcome pool side aperitivo and bike fitting session. Let’s enjoy the welcome dinner at La Porta.

Sunday : Pienza, Montepulciano

First stage is Pienza, a pristine Renaissance jewel created in 1458. Pope Pius II chose the famous Florentine architect Rossellino to transform his home village of Corsignano into one of the few examples left of 15th century architecture. The main product is the pecorino the delicious pungent cheese made using only sheep milk – continue to next village Montepulciano known as the Pearl of the Sixteenth Century, do not miss the visit at underground wine cellar and have a short taste “nobile” wine. Back in the saddle last stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where you bike through the fields that inspired Renaissance painters. Back by van for your first cooking session

Monday: Montalcino & Brunello

First stop is the ancient Roman spa of Bagno Vignoni. Legend has it that Saint Catherine and Pope Pius II both bathed in the thermal waters here. You can take off your shoes and dip your toes in the rivulets that come warm from the earth. Time a short visit to Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne. The hill town is very famous for Brunello wine made with the Sangiovese Grosso grape and aged a minimum of four years. End of ride at Ciacci Piccolomini for a Wine tasting, you will savor brunello wine and learn about the aging.

Tuesday : Cortona

After breakfast ready to start: leave by bike from the villa and reach Montepulciano after some few uphills, once here the ride continue with a long nice downhill and will be flat “the Val di Chiana” once a swampy lowland, except for the final climb to reach the old town on the hill Cortona: one’s of Italy's oldest towns. The first set of city walls were built by the Etruscans in the 4th century BC. It became famous by Frances Mayes in her bestselling book “Under the Tuscan sun” also a movie!! Dinner at Dopolavoro della Foce.

Wednesday: Radicofani & pici

Today another terrific bike ride : start from villa reach Radicofani a medieval and enchanting village with a 1000 dating Rocca, one of the most impressive fortresses in Tuscany. Enjoy the downhill back to the valley: our destination is the Mulino Val d’Orcia! It rise along Francigena road near the old Spedaletto Castle, shelter for wayfarer which, in the Middle Ages, wanted to get to Rome from all over Europe, in the XV century. Castle was readapted in a granary, a real fortified farm. You will visit the stone mill and have a hands-on cooking lesson about hand rolled pasta of this region: the pici . Let’s learn the classic aglione sauce: tomato and spring garlic and after have the lunch under the pergola – ride back to the villa only 8 km. Dinner at the villa with pecorino cheese tasting

Thursday: Siena & Le Crete

After breakfast departure by bike from the villa. First stop is San Quirico, an Etruscan origin village with a superb example of the Italian garden: the Horti Leonini. Pass through Asciano and Le crete area, with strange rock formations and lone farmhouse flanked by twin cypress tree. Let’s pedal through vineyards and forest and arrive in Siena. Go soon to visit the shell shape square where the Palio horserace is run and enjoy a free lunch on your own. Back to the villa, time for jump in the pool and rest. Our farewell dinner at restaurant at la bandita townhouse

Arrivederci al prossimo bike tour

After a breakfast all together we arrange transfer to Chiusi train station.
Podere Palazzo Dell'Orcia
The Palazzo dell’Orcia farmhouse was built in the thirties by the Marchesa Origo - La Foce - replacing an old inn where the Eminences used to rest when they were going through the nearby Francigena road.

Podere Palazzo Dell'Orcia - Room
Furnished with rustic antiques, the Villa has a warm atmosphere of an authentic villa with Tuscan charm.
The Villa has 9 double/twin bedrooms With en suite facilities with both showers and baths
Podere Palazzo Dell'Orcia - Garden
The Villa stands in the centre of the natural reserve of Lucciola Bella, in the heart of the Orcia valley - Unesco site sicne 2004
Podere Palazzo Dell'Orcia - Overwiev
This marvelous 17th century Villa belongs to a large estate property of Nardi enzo
Podere Palazzo Dell'Orcia - Pool
The pool will be open May through September.
Podere Palazzo Dell'Orcia - Breakfast
Nowadays, the Company owns 100 ha cultivated with cereals and wheat which is mainly used for the Chianina-breeding. This activity is, among others, the most important one.
Podere Palazzo Dell'Orcia - room
From the vineyards a wonderful red DOC Orcia wine is produced. Of course, it is available to be tasted for all our kind guests. They produce wine, olive oil, Chianina meat.

Cycling Tuscany

bike tour Tuscany
cooking lesson in Italy
culinary bike trip Tuscany
cycling trip Cortona
foody bike tour italy
Italy bicycling vacation
montalcino bike trips
tuscan countryside bike trip
chianti cycling

Price & Inclusions

Cost: Euro 2800 per person in double occupancy
Single room supplement euro 490

Six nights in villa with all breakfasts
Six dinners & one lunch
Three cooking classes
One wine tasting
One cheese tasting
All maps, trip notes and detailed route directions
All Shuttles and technical assistance
Van support
Experienced English speaking guide
Cicloposse water bottle
Transfer on day one from station
Transfer on day seven to the station
Sales taxes

Not included
Airfare to Italy, train to Chiusi, 5 lunches, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature

Bike Rental per entire tour
Hybrid bike euro 140
Race bike     euro 180
E-bike          euro 180


Tour Reviews

26 ottobre 2016

We had a absolutely fantastic time. I expected the riding to be great but had no idea all the rest of it the week would be so wonderful. Boscarello is beautiful, of course, but in addition Carlotta was a wonderful hostess and it was exciting to meet her father as well. The food was delicious — we’re still remembering and talking about the recipies! You and Marco were absolutely the best! All the riding details we so well thought out — we loved the restaurants and the visits. It was perfecto!! Thanks very much for everything. We really look forward to doing it again!

26 ottobre 2016

Giuliana and Marco Wanted to thank you for a fabulous time in Tuscany. Jeff’s first trip to Europe and my first to Tuscany was made fabulously memorable and that is thanks to you both. We were so pleasantly surprised by the accommodations, by Duccoi, his family and staff and by your professional yet fun expertise and by everyone who helped make our experience so enjoyable. We will be return customers – guaranteed! (keep us in mind for Croatia for next September!) Gracie once again – Arrivederci fino alla prossima Volta!

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